Simple Unix Wordpress and Outlook Problem

I have an Ubuntu non-managed VPS server that is currently running Wordpress for the (3) sites hosted on it. I also use Webmin/Virtualmin, so you must have experience with these. I am having the following issues I need help with: 1.) Everything was working fine, as I added 1 new posting with photos today to each site. However, upon adding article number 2 to each site, only 1/2 of the photos upload and the remainder return an HTTP Error in the upload manager... I read some sources online and tried those tips, but nothing worked, so here I am! The files are JPG and PNG only, and aren't large... I never had these issues before and I haven't changed anything to have caused this. 2.) I was having some email issues for a few days, as emails were not coming over to Outlook, but they would hit the server. Today it randomly started working and pulled all my old emails through to the Outlook program, but now I just sent a Test email to my account, and it shows on the server, but doesn't pull to outlook. I don't understand why this is happening... The sync goes through 100% with no errors.... I need someone that has experience with UNIX, Non-managed servers, Wordpress, and Webmin/Virtualmin. Thanks!